XMap on the PocketPC stores its waypoints in individual .wpt files.
For example, waypoints generated by XMap on the PocketPC are stored
by default in the "My Documents" folder using the sequential names
"XMap1.wpt", "XMap2.wpt", ad nauseum. Needless to say, this is not very
efficient.

As writing multiple waypoint files is outside of the scope of GPSBabel,
GPSBabel chooses to write one big file, one waypoint per line.
Extracting lines from this file is left as an exercise for the end user.
A simple Perl script to handle this conversion is included at the end
of this chapter.

It should also be noted that reading multiple files
is indeed possible, but if you have more than a few points, it can be a task.
For example:

will read the two Xmap .wpt files and write one mapsend file. This
is fine for a small handful of points, but could be quite cumbersome
for folks like me who have 100+ waypoints loaded into XMap. For *nix
folks, something as simple as: